Recombinagenic activity of integerrimine, a pyrrolizidine alkaloid from Senecio brasiliensis, in somatic cells of Drosophila melanogaster

Environmental and Molecular Mutagenesis

Volumn 29, Issue 1, 1997, Pages 91-97

  Campesato, Viviane Ribeiro ^a   Graf, Ulrich ^b   Reguly, Maria Luiza ^a   Rodrigues De Andrade, Heloisa Helena ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Drosophila melanogaster; Genotoxicity; Integerrimine; Mitotic recombination; Pyrrolizidine alkaloids; Somatic cells

Indexed keywords

INTEGERRIMINE; PYRROLIZIDINE ALKALOID;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DROSOPHILA MELANOGASTER; GENETIC RECOMBINATION; GENOTOXICITY; NONHUMAN; REGRESSION ANALYSIS; SOMATIC CELL; SOMATIC MUTATION; TAXONOMY;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CROSSES, GENETIC; DROSOPHILA MELANOGASTER; FEMALE; HETEROZYGOTE; INVERSION, CHROMOSOME; LARVA; MALE; MITOSIS; MUTAGENICITY TESTS; MUTATION; PLANTS, TOXIC; PYRROLIZIDINE ALKALOIDS; RECOMBINATION, GENETIC; SENECIO; SENSITIVITY AND SPECIFICITY; WING;

ANIMALIA; DROSOPHILA MELANOGASTER; MELANOGASTER; SENECIO BRASILIENSIS;

EID: 1842407216     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(1997)29:1<91::AID-EM12>3.0.CO;2-C     Document Type: Article

References (50)

1. Butler W, Mattocks AR, Barnes JM (1970): Lesions in the liver and lungs of rats given pyrrole derivatives of pyrrolizidine alkaloids. J Pathol 100:169-175.
2. Chies JM, Marques EK (1980): Ação mutagénica da integerrimina sobre os índices mitóticos dos meristemas radiculares do Allium cepa. Ciênc Cult 32:682.
3. Chung WG, Buhler DR (1994): The effect of spironolactone treatment on the cytochrome P450-mediated metabolism of the pyrrolizidine alkaloid senecionine by hepatic microsomes from rats and guinea pigs. Toxicol Appl Pharmacol 127:314-319.
4. Chung WG, Miranda CL, Buhler DR (1995): A cytochrome P4502B form is the major bioactivation enzyme for the pyrrolizidine alkaloid senecionine in the guinea pig. Xenobiotica 25:929-939.
5. Clark AM (1959): Mutagenic activity of the alkaloid heliotrine in Drosophila. Nature 183:731-732.
6. Clark AM (1976): Naturally occurring mutagens. Mutat Res 32:361-374.
7. Feyereisen R (1993): Cytochrome P450 in insects. In Schenkman JB, Gram H (eds): "Cytochrome P450." Berlin: Springer-Verlag, pp 311-324.
8. Feyereisen R, Koener JF, Farnsworth DE, Nebert DW (1989): Isolation and sequence of cDNA encoding a cytochrome P-450 from an insecticide-resistant strain of the house fly Musca domestica. Proc Natl Acad Sci USA 86:1465-1469.
9. Frei H, Würgler FE (1988): Statistical methods to decide whether mutagenicity test data from Drosophila assays indicate a positive, negative, or inconclusive result. Mutat Res 203:297-308.
10. Frei H, Lüthy J, Brauchli J, Zweifel U, Würgler FE, Schlatter C (1992): Structure/activity relationships of the genotoxic potencies of siteen pyrrolizidine alkaloids assayed for the induction of somatic mutation and recombination in wing cells of Drosophila melanogaster. Chem Biol Interact 83:1-22.
11. Frölich A, Würgler FE (1989): New tester strains with improved high bioactivation capacity tor the Drosophila wing spot test. Mutat Res 216:179-187.
12. Gimmler-Luz MC (1993): Genotoxicidade do alcalóide integerrimina extraído de Senecio brasiliensis em camundongos. PhD thesis, Porto Alegre, Brazil.
13. Gimmler-Luz MC, Marques EK, Johnston RC (1987): Action of the pyrrolizidine alkaloid integerrimine in inducing meiotic chromosome aberrations in male mice. Rev Brasil Genet 10:31-41.
14. Gimmler-Luz MC, Erdtmann B, Balbueno RA (1990): The effect of the pyrrolizidine alkaloid integerrimine on the chromosomes of mouse bone marrow cells. Mutat Res 241:297-304.
15. Graf U (1995): Analysis of the relationship between age of larvae at mutagen treatment and frequency and size of spots in the wing somatic mutation and recombination test in Drosophila melanogaster. Experientia 51:168-173.
16. Graf U, van Schaik N (1992): Improved high bioactivation cross for the wing somatic mutation and recombination test in Drosophila melanogaster. Mutat Res 271:59-67.
17. Graf U, Würgler FE (1996): The somatic white-ivory eye spot test does not detect the same spectrum of genotoxic events as the wing somatic mutation and recombination test in Drosophila melanogaster. Environ Mol Mutagen 27:219-226.
18. Graf U, Würgler FE, Katz AJ, Frei H, Juon H, Hall CB, Kale PG (1984): Somatic mutation and recombination test in Drosophila melanogaster. Environ Mutagen 6:153-188.
19. Graf U, Frei H, Kägi A, Katz AJ, Würgler FE (1989): Thirty compounds tested in the Drosophila wing spot test. Mutat Res 222:359-373.
20. Graf U, Heo O, Olvera Ramirez O (1992): The genotoxicity of chromium(VI) oxide in the wing spot test of Drosophila melanogaster is over 90% due to mitotic recombination. Mutat Res 266:197-203.
21. Griffin DS, Segall HJ (1986): Genotoxicity and cytotoxicity of selected pyrrolizidine alkaloids, a possible alkenal metabolite of the alkaloids and related alkenals. Toxicol Appl Pharmacol 86:227-234.
22. Guengerich FP (1995): Human cytochrome P450 enzymes. In Ortiz de Montellano PR (ed): "Cytochrome P450: Structure, Mechanism and Biochemistry," 2nd ed. New York: Plenum Press, pp 473-535.
23. Hincks JR, Kim H-J, Segall HJ, Molyneux RJ, Stermitz FR, Coulombe RA, Jr (1991): DNA cross-linking in mammalian cells by pyrrolizidine alkaloids: Structure-activity relationships. Toxicol Appl Pharmacol 111:90-98.
24. Huxtable RJ (1980): Herbal teas and toxins: Novel aspects of pyrrolizidine poisoning in the United States. Perspect Biol Med 24:1-14.
25. Kastenbaum MA, Bowman KO (1970): Tables for determining the statistical significance of mutation frequencies. Mutat Res 9:527-549.
26. Koekemoer MJ, Warren FL (1951): The Senecio alkaloids. Part VIII. The occurrence and preparation of the N-oxides: An improved method of extraction of the Senecio alkaloids. J Chem Soc CI951:66-68.
27. Koletsky A, Oyasu R, Reddy JK (1978): Mutagenicity of the pyrrolizidine (Senecio) alkaloid, lasiocarpine, in the Salmonella/microsome test. Lab Invest 38:352.
28. Lindsley DL, Zimm GG (eds) (1992): "The Genome of Drosophila melanogaster." San Diego, CA: Academic Press.
29. Mattocks AR (1986): "Chemistry and Toxicology of Pyrrolizidine Alkaloids." London: Academic Press.
30. Moraes ECF (1952): Contribuição ao estudo químico-toxicológico do Senecio brasiliensis Less. "Livre Docência." Doctoral thesis, Faculdade de Farmácia e Odontologia da USP, São Paulo, Brazil.
31. Mori H, Sugie S, Yoshimi N, Asada Y, Furuya T, Williams GM (1985): Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse and hamster hepatocytes. Cancer Res 45:3125-3129.
32. Motidome M, Ferreira PC (1966): Alcaloídes do Senecio brasiliensis Less. Rev Fac Farm Bioquim (USP) 4:13-44.
33. Paula-Ramos ALL (1986): Efeitos genotóxico, mutagênico e recombinogênico de alcalóides pirrolizidínicos de gênero Senecio, em células procarióticas e eucarióticas. PhD thesis, Porto Alegre, Brazil.
34. Paula-Ramos ALL, Marques EK (1978): Mutagenic action of integerrimine, an alkaloid present in Senecio brasiliensis (Sprengel) Less., in Drosophila. Rev Brasil Genet 1:279-287.
35. Paula-Ramos ALL, Querol CB, Marques EK, Henriques JAP (1991): Cytotoxic activation of the pyrrolizidine alkaloid integerrimine in the yeast Saccharomyces cerevisiae is caused by repairable DNA damage. Rev Brasil Genet 4:897-912.
36. Ramsdell HS, Buhler DR (1987): Microsomal metabolism of pyrrolizidine alkaloids: N-Oxidation of seneciphylline and senecionine. Toxicol Lett 37:241-249.
37. 2 in deoxyguanosine by dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline. Cancer Res 42:8-14.
38. Robertson K, Seymour JL, Hsia MT, Allen JR (1977): Covalent interaction of the dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione. Cancer Res 37:3141-3144.
39. Rocha CLMSC, Azevedo JL (1986): Use of the meth G1 reversion system of Aspergillus nidulans for the detection of mutagenicity of the alkaloid integerrimine. Rev Brasil Genet 9:393-405.
40. Rodriguez-Arnaiz R, Orozco Soto P, Gaytán Oyarzún JC, Graf U (1996): Analysis of mitotic recombination induced by several mono- and bifunctional alkylating agents in the Drosophila wing-spot test. Mutat Res 351:133-146.
41. Rubiolo P, Pieters L, Calomme M, Bicchi C, Vlietnick A, van den Berghe D (1992): Mutagenicity of pyrrolizidine alkaloids in the Salmonella typhimurium/mammalian microsome system. Mutat Res 281:143-147.
42. Saner C (1995): "Characterization of Drosophila melanogaster Cytochrome P450 6A2: Gene Structure, Expression Pattern and Metabolic Capacity Towards Procarcinogens." Thesis 11205, Swiss Federal Institute of Technology, Zurich, Switzerland.
43. Saner C, Weibel B, Würgler FE, Sengstag C (1996): Metabolism of promutagens catalyzed by Drosophila melanogaster CYP6A2 enzyme in Saccharomyces cerevisiae. Environ Mol Mutagen 27:46-58.
44. Schoental R (1968): Chemical structure and pathological effects of pyrrolizidine alkaloids. Israel J Med Sci 4:1133-1145.
45. Schoental R (1982): Health hazards of pyrrolizidine alkaloids: A short review. Toxicol Lett 10:323-326.
46. Smith LW, Culvenor CCJ (1981): Plant sources of hepatotoxic pyrrolizidine alkaloids. J Natl Prod 44:129-152.
47. Szabad J, Soos I, Polgar G, Hejja G (1983): Testing the mutagenicity of malondialdehyde and formaldehyde by the Drosophila mosaic and the sex-linked recessive lethal tests. Mutat Res 113:117-133.
48. Takanashi H, Umeda M, Hirono I (1980): Chromosomal aberrations and mutation in cultured mammalian cells induced by pyrrolizidine alkaloids. Mutat Res 78:67-77.
49. Williams DE, Reed RL, Kedzierski B, Dannan GA, Guengerich, FP (1989): Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver. Drug Metab Disp 17:387-392.
50. Winter CK, Segall HJ, Jones AD (1988): Species differences in the hepatic microsomal metabolism of the pyrrolizidine alkaloid senecionine. Comp Biochem Physiol C 90:429-433.